Selank

Chemical compound

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|

Pharmaceutical compound

Selank

Clinical data
Other names| Selanc; L-threonyl-L-lysyl-L-prolyl-L-arginyl-L-prolylglycyl-L-Proline
Routes of
administration| Nasal muscosa, IV
Legal status
Legal status|

* In general: unscheduled

Identifiers

IUPAC name

* 1-[2-({1-[2-({1-[6-Amino-2-(2-amino-3-hydroxy-butyrylamino)-hexanoyl]-pyrrolidine-2-carbonyl}-amino)-5-guanidino-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-acetyl]-pyrrolidine-2-carboxylic acid

CAS Number|

* 129954-34-3 N

PubChem CID|

* 11765600

ChemSpider|

* 9940290 Y

UNII|

* TS9JR8EP1G

CompTox Dashboard (EPA)|

* DTXSID701029276

Chemical and physical data
Formula| C33H57N11O9
Molar mass| 751.887 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* NCCCCC(C(=O)N1CCCC1C(=O)NC(C(=O)N2CCCC2C(=O)NCC(=O)N3CCCC3C(=O)O)CCCNC(=N)N)NC(C(C(C)O)N)=O

InChI

* InChI=1S/C33H57N11O9/c1-19(45)26(35)29(49)41-20(8-2-3-13-34)30(50)44-17-6-11-23(44)28(48)40-21(9-4-14-38-33(36)37)31(51)43-16-5-10-22(43)27(47)39-18-25(46)42-15-7-12-24(42)32(52)53/h19-24,26,45H,2-18,34-35H2,1H3,(H,39,47)(H,40,48)(H,41,49)(H,52,53)(H4,36,37,38)/t19-,20+,21+,22+,23+,24+,26+/m1/s1 Y

* Key:JTDTXGMXNXBGBZ-UHFFFAOYSA-N N

NY (what is this?) (verify)

Selank (Russian: Cеланк) is a nootropic anxiolytic peptide based drug developed by the Institute of Molecular Genetics of the Russian Academy of Sciences. Selank is a heptapeptide with the sequence Thr-Lys-Pro-Arg-Pro-Gly-Pro (TKPRPGP). It is a synthetic analogue of the human tuftsin.

## Pharmacology

[edit]

Selank is a synthetic analogue of the immunomodulatory peptide tuftsin; as such, it mimics many of its effects. It has been shown to modulate the expression of Interleukin-6 (IL-6) and affect the balance of T helper cell cytokines.[1] It has been shown to influence the concentration of monoamine neurotransmitters[2] and induce metabolism of serotonin.[3][4] Selank has also been found to rapidly elevate the expression of brain-derived neurotrophic factor (BDNF) in the hippocampus of rats.[5]

Selank, as well as a related peptide drug, Semax, have been found to inhibit enzymes involved in the degradation of enkephalins and other endogenous regulatory peptides, and this action may be involved in their effects.[6] It has also been found to affect the activity of carboxypeptidase H and phenylmethylsulfonylfluoride-inhibited carboxypeptidase in rat nervous system tissue.[7]

Selank has been found to produce antidepressant-like effects in animal models of depression and anhedonia.[8]

## Clinical trials

[edit]

In clinical trials, the drug has shown to provide a sustained nootropic and anxiolytic effect which is useful for the treatment of generalized anxiety disorder (GAD).[1] Selank has an advantage over traditional anxiety treatments, such as benzodiazepines and barbiturates, as it has no sedating or negative cognitive side effects and no associated addiction or withdrawal problems.[citation needed]

Selank is closely related to another nootropic drug, Semax, also developed by the Institute of Molecular Genetics in Russia. This drug is currently available in Russian and Ukrainian pharmacies.[9]

As with all lyophilized peptides, it needs refrigeration to remain stable within sterile water solutions, such as bacteriostatic water concentrations.

## See also

[edit]

* Afobazole
* Mebicar
* Semax
* Bemethyl
* List of Russian drugs

## References

[edit]

1. ^ a b Uchakina ON, Uchakin PN, Miasoedov NF, Andreeva LA, Shcherbenko VE, Mezentseva MV, et al. (2008). "[Immunomodulatory effects of selank in patients with anxiety-asthenic disorders]". Zhurnal Nevrologii I Psikhiatrii imeni S.S. Korsakova. 108 (5): 71–75\. PMID 18577961.
2. ^ Narkevich VB, Kudrin VS, Klodt PM, Pokrovskiĭ AA, Kozlovskaia MM, Maĭskiĭ AI, Raevskiĭ KS (2008). "[Effects of heptapeptide selank on the content of monoamines and their metabolites in the brain of BALB/C and C57Bl/6 mice: a comparative study]". Eksperimental'naia i Klinicheskaia Farmakologiia. 71 (5): 8–12\. PMID 19093364.
3. ^ Semenova TP, Kozlovskiĭ II, Zakharova NM, Kozlovskaia MM (August 2010). "[Experimental optimization of learning and memory processes by selank]". Eksperimental'naia i Klinicheskaia Farmakologiia. 73 (8): 2–5\. PMID 20919548.
4. ^ Semenova TP, Kozlovskiĭ II, Zakharova NM, Kozlovskaia MM (2009). "[Comparison of the effects of selank and tuftsin on the metabolism of serotonin in the brain of rats pretreated with PCPA]". Eksperimental'naia i Klinicheskaia Farmakologiia. 72 (4): 6–8\. PMID 19803361.
5. ^ Inozemtseva LS, Karpenko EA, Dolotov OV, Levitskaya NG, Kamensky AA, Andreeva LA, Grivennikov IA (2008). "Intranasal administration of the peptide Selank regulates BDNF expression in the rat hippocampus in vivo". Doklady Biological Sciences. 421: 241–243\. doi:10.1134/s0012496608040066. PMID 18841804. S2CID 40709909.
6. ^ Kost NV, Sokolov OI, Gabaeva MV, Grivennikov IA, Andreeva LA, Miasoedov NF, Zozulia AA (2001). "Semax and selank inhibit the enkephalin-degrading enzymes from human serum". Bioorganicheskaia Khimiia (in Russian). 27 (3): 180–183\. doi:10.1023/A:1011373002885. PMID 11443939. S2CID 26029820.
7. ^ Solov'ev VB, Gengin MT, Sollertinskaia TN, Latynova IV, Zhivaeva LV (2012). "[Effect of selank on the main carboxypeptidases in the rat nervous tissue]". Zhurnal Evoliutsionnoi Biokhimii I Fiziologii (in Russian). 48 (3): 254–257\. PMID 22827026.
8. ^ Sarkisova KI, Kozlovskiĭ II, Kozlovskaia MM (2008). "[Effects of heptapeptide selank on genetically-based and situation-provoked symptoms of depression in behavior in WAG/Rij and Wistar rats, and in BALB/c mice]". Zhurnal Vysshei Nervnoi Deiatelnosti imeni I P Pavlova (in Russian). 58 (2): 226–237\. PMID 18661785.
9. ^ "СЕМАКС: лекарственное средство широкого спектра действия эффективный стимулятор нервной системы" [SEMAX: a broad-spectrum drug effective stimulant of the nervous system]. Institute of Molecular Genetics (in Russian). Moscow. Archived from the original on 2011-07-22.

## External links

[edit]

* Selank instructions

* v
* t
* e

Anxiolytics (N05B)

5-HT1ARTooltip 5-HT1A receptor agonists|

* Buspirone
* Gepirone
* Tandospirone

GABAARTooltip GABAA receptor PAMsTooltip positive allosteric modulators|

* Benzodiazepines: Adinazolam
* Alprazolam
* Bromazepam
* Camazepam
* Chlordiazepoxide
* Clobazam
* Clonazepam
* Clorazepate
* Clotiazepam
* Cloxazolam
* Diazepam#
* Ethyl loflazepate
* Etizolam
* Fludiazepam
* Halazepam
* Ketazolam
* Lorazepam#
* Medazepam
* Nordazepam
* Oxazepam
* Pinazepam
* Prazepam; Others: Alpidem‡
* Barbiturates (e.g., phenobarbital)
* Carbamates (e.g., meprobamate)
* Carisoprodol
* Chlormezanone‡
* Ethanol (alcohol)
* Etifoxine

Gabapentinoids
(α2δ VDCC blockers)|

* Gabapentin
* Gabapentin enacarbil
* Phenibut
* Pregabalin

Antidepressants|

* SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram)
* SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine)
* SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone)
* TCAsTooltip Tricyclic antidepressants (e.g., clomipramine#)
* TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine)
* MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine
* Bupropion
* Tianeptine
* Vilazodone
* Vortioxetine

Sympatholytics
(Antiadrenergics)|

* Alpha-1 blockers (e.g., prazosin)
* Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine)
* Beta blockers (e.g., propranolol, atenolol, betaxolol, nadolol, oxprenolol, pindolol)

Others|

* Benzoctamine
* Cycloserine
* Fabomotizole
* Hydroxyzine
* Lorpiprazole
* Mebicar
* Mepiprazole
* Nicotine (tobacco)
* Opipramol
* Oxaflozane‡
* Phenaglycodol
* Phenibut
* Picamilon
* Selank
* Tiagabine
* Tofisopam
* Validolum

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Opioid receptor modulators

μ-opioid
(MOR)|

| Agonists
(abridged;
full list)|

* 3-HO-PCP
* 7-Acetoxymitragynine
* 7-Hydroxymitragynine
* ψ-Akuammigine
* α-Chlornaltrexamine
* α-Narcotine
* Acetyldihydrocodeine
* Acetylfentanyl
* Acrylfentanyl
* Adrenorphin (metorphamide)
* AH-7921
* Akuammicine
* Akuammidine
* Alfentanil
* Anileridine
* Apparicine
* β-Endorphin
* BAM-12P
* BAM-18P
* BAM-22P
* Benzhydrocodone
* Benzylmorphine
* Bezitramide
* Biphalin
* BU08070
* Buprenorphine
* Butorphan
* Butorphanol
* Butyrfentanyl
* BW373U86
* Carfentanil
* Casokefamide
* Cebranopadol
* Chloroxymorphamine
* Codeine
* DADLE
* DAMGO (DAGO)
* Dermorphin
* Desmetramadol (desmethyltramadol)
* Desomorphine
* Deumitragynine
* Dextromoramide
* Dextropropoxyphene (propoxyphene)
* Dezocine
* Dimenoxadol
* Dimethylaminopivalophenone
* Eluxadoline
* Diamorphine (heroin)
* Dihydrocodeine
* Dihydroetorphine
* Dihydromorphine
* Dinalbuphine sebacate
* Diphenoxylate
* Dipipanone
* Dynorphin A
* Embutramide
* Endomorphin-1
* Endomorphin-2
* Eseroline
* Ethylmorphine
* Etorphine
* Fentanyl
* Fluorophen
* Frakefamide
* Furanylfentanyl
* Hemorphin-4
* Herkinorin
* Hodgkinsine
* Hydrocodone
* Hydromorphinol
* Hydromorphone
* IBNtxA
* Ketamine
* Ketobemidone
* Kratom
* Laudanosine
* Lefetamine
* Leu-enkephalin
* Levacetylmethadol
* Levomethorphan
* Levorphanol
* Lexanopadol
* Loperamide
* Loxicodegol
* LS-115509
* Matrine
* Meptazinol
* Met-enkephalin (metenkefalin)
* Methadone
* Metkefamide
* Metopon
* Mitragynine
* Mitragynine pseudoindoxyl
* Morphiceptin
* Morphine
* Nalbuphine
* Naloxone benzoylhydrazone (NalBzOH)
* Nalmexone
* Naltalimide
* Neopine
* NFEPP
* Nicocodeine
* Nicodicodine
* Nicomorphine
* Norketamine
* Nufenoxole
* Octreotide
* Oliceridine
* Oxycodegol
* Oxymorphone-3-methoxynaltrexonazine (OM-3-MNZ)
* Oripavine
* Oxycodone
* Oxymorphazone
* Oxymorphonazine
* Oxymorphone
* Oxymorphone phenylhydrazone
* OxyPNPH
* Papaver somniferum (opium)
* Pentazocine
* Pericine
* Pethidine (meperidine)
* Phenazocine
* Phencyclidine
* Piminodine
* Piritramide
* PL-017
* Prodine
* Propiram
* PZM21
* Racemethorphan
* Racemorphan
* Remifentanil
* Salsolinol
* SC-17599
* Sinomenine
* Sufentanil
* Tapentadol
* Tetrahydropapaveroline
* TH-030418
* Thebaine
* Thienorphine
* Tianeptine
* Tilidine
* Tramadol
* Trimebutine
* TRIMU 5
* TRV734
* Tubotaiwine
* U-47700
* Valorphin
* Viminol
* Xorphanol

|

Antagonists|

* (3S,4S)-Picenadol
* 2-(S)-N,N-(R)-Viminol
* 3CS-nalmefene
* 4-Caffeoyl-1,5-quinide
* 4′-Hydroxyflavanone
* 4',7-Dihydroxyflavone
* 6β-Naltrexol
* 6β-Naltrexol-d4
* 18-MC
* α-Gliadin
* β-Chlornaltrexamine
* β-Funaltrexamine
* Akuammine
* Alvimopan
* AM-251
* Apigenin
* AT-076
* Axelopran
* Bevenopran
* Catechin
* Catechin gallate
* Clocinnamox
* CTAP
* CTOP
* Cyclofoxy
* Cyprodime
* Diacetylnalorphine
* Diprenorphine
* ECG
* EGC
* Epicatechin
* Eptazocine
* Gemazocine
* Ginsenoside R
* Hyperoside
* Ibogaine
* JDTic
* Levallorphan
* Lobeline
* LY-255582
* LY-2196044
* Methocinnamox
* Methylnaltrexone
* Methylsamidorphan chloride
* Naldemedine
* Nalmefene
* Nalodeine (N-allylnorcodeine)
* Nalorphine
* Nalorphine dinicotinate
* Naloxazone
* Naloxegol
* Naloxol
* Naloxonazine
* Naloxone
* Naltrexazone
* Naltrexonazine
* Naltrexone
* Naltrindole
* Naringenin
* Noribogaine
* Oxilorphan
* Pawhuskin A
* Rimonabant
* Quadazocine
* Samidorphan
* Taxifolin

δ-opioid
(DOR)|

| Agonists|

* 3CS-nalmefene
* 6'-GNTI
* 7-SIOM
* ADL-5747 (PF-04856881)
* ADL-5859
* Alazocine (SKF-10047)
* Amoxapine
* AR-M100390 (ARM390)
* AZD2327
* β-Endorphin
* BAM-18P
* Biphalin
* BU-48
* Butorphan
* Butorphanol
* BW373U86
* Casokefamide
* Cebranopadol
* Codeine
* Cyclazocine
* DADLE
* Deltorphin A
* Deltorphin I
* Deltorphin II
* Desmethylclozapine
* Desmetramadol (desmethyltramadol)
* Dezocine
* Diamorphine (heroin)
* Dihydroetorphine
* Dihydromorphine
* DPDPE
* DPI-221
* DPI-3290
* DSLET
* Ethylketazocine
* Etorphine
* Fentanyl
* FIT
* Fluorophen
* Hemorphin-4
* Hydrocodone
* Hydromorphone
* Ibogaine
* Isomethadone
* JNJ-20788560
* KNT-127
* Kratom
* Laudanosine
* Leu-enkephalin
* Levomethorphan
* Levorphanol
* Lexanopadol
* Lofentanil
* Met-enkephalin (metenkefalin)
* Metazocine
* Metkefamide
* Mitragynine
* Mitragynine pseudoindoxyl
* Morphine
* N-Phenethyl-14-ethoxymetopon
* Norbuprenorphine
* NalBzOH
* Oripavine
* Oxycodone
* Oxymorphone
* Pethidine (meperidine)
* Proglumide
* Racemethorphan
* Racemorphan
* RWJ-394674
* Samidorphan
* SB-235863
* SNC-80
* SNC-162
* TAN-67 (SB-205,607)
* TH-030418
* Thebaine
* Thiobromadol (C-8813)
* Tonazocine
* Tramadol
* TRV250
* Xorphanol
* Zenazocine

|

Antagonists|

* 4',7-Dihydroxyflavone
* 5'-NTII
* 6β-Naltrexol
* 6β-Naltrexol-d4
* α-Santolol
* β-Chlornaltrexamine
* Apigenin
* AT-076
* Axelopran
* Bevenopran
* BNTX
* Catechin
* Catechin gallate
* Clocinnamox
* Diacetylnalorphine
* Diprenorphine
* ECG
* EGC
* Eluxadoline
* Epicatechin
* ICI-154129
* ICI-174864
* LY-255582
* LY-2196044
* Methylnaltrexone
* Methylnaltrindole
* N-Benzylnaltrindole
* Nalmefene
* Nalorphine
* Naltrexone
* Naltriben
* Naltrindole
* Naloxone
* Naringenin
* Noribogaine
* Pawhuskin A
* Quadazocine
* SDM25N
* SoRI-9409
* Taxifolin
* Thienorphine

κ-opioid
(KOR)|

| Agonists|

* 3CS-nalmefene
* 6'-GNTI
* 8-CAC
* 18-MC
* 14-Methoxymetopon
* β-Chlornaltrexamine
* β-Funaltrexamine
* Adrenorphin (metorphamide)
* Akuammicine
* Alazocine (SKF-10047)
* Allomatrine
* Apadoline
* Asimadoline
* BAM-12P
* BAM-18P
* BAM-22P
* Big dynorphin
* Bremazocine
* BRL-52537
* Butorphan
* Butorphanol
* BW373U86
* Cebranopadol
* Ciprefadol
* CR665
* Cyclazocine
* Cyclorphan
* Cyprenorphine
* Desmetramadol (desmethyltramadol)
* Diamorphine (heroin)
* Diacetylnalorphine
* Difelikefalin
* Dihydroetorphine
* Dihydromorphine
* Dinalbuphine sebacate
* Diprenorphine
* Dynorphin A
* Dynorphin B (rimorphin)
* Eluxadoline
* Enadoline
* Eptazocine
* Erinacine E
* Ethylketazocine
* Etorphine
* Fedotozine
* Fentanyl
* Gemazocine
* GR-89696
* GR-103545
* Hemorphin-4
* Herkinorin
* HS665
* Hydromorphone
* HZ-2
* Ibogaine
* ICI-199,441
* ICI-204,448
* Ketamine
* Ketazocine
* Laudanosine
* Leumorphin (dynorphin B-29)
* Levallorphan
* Levomethorphan
* Levorphanol
* Lexanopadol
* Lofentanil
* LPK-26
* Lufuradom
* Matrine
* MB-1C-OH
* Menthol
* Metazocine
* Metkefamide
* Mianserin
* Mirtazapine
* Morphine
* Moxazocine
* MR-2034
* N-MPPP
* Nalbuphine
* NalBzOH
* Nalfurafine
* Nalmefene
* Nalodeine (N-allylnorcodeine)
* Nalorphine
* Naltriben
* Niravoline
* Norbuprenorphine
* Norbuprenorphine-3-glucuronide
* Noribogaine
* Norketamine
* Oripavine
* Oxa-noribogaine
* Oxilorphan
* Oxycodone
* Pentazocine
* Pethidine (meperidine)
* Phenazocine
* Proxorphan
* Racemethorphan
* Racemorphan
* RB-64
* Salvinorin A (salvia)
* Salvinorin B ethoxymethyl ether
* Salvinorin B methoxymethyl ether
* Samidorphan
* Spiradoline (U-62066)
* TH-030418
* Thienorphine
* Tifluadom
* Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
* U-50488
* U-54494A
* U-69593
* Xorphanol

|

Antagonists|

* 4′-Hydroxyflavanone
* 4',7-Dihydroxyflavone
* 5'-GNTI
* 6'-GNTI
* 6β-Naltrexol
* 6β-Naltrexol-d4
* β-Chlornaltrexamine
* Buprenorphine/samidorphan
* Amentoflavone
* ANTI
* Apigenin
* Arodyne
* AT-076
* Aticaprant
* Axelopran
* AZ-MTAB
* Binaltorphimine
* BU09059
* Buprenorphine
* Catechin
* Catechin gallate
* CERC-501 (LY-2456302)
* Clocinnamox
* CVL-354
* Cyclofoxy
* Dezocine
* DIPPA
* EGC
* ECG
* Epicatechin
* Hyperoside
* JDTic
* LY-255582
* LY-2196044
* LY-2444296
* LY-2459989
* LY-2795050
* MeJDTic
* Methylnaltrexone
* ML190
* ML350
* MR-2266
* N-Fluoropropyl-JDTic
* Naloxone
* Naltrexone
* Naltrindole
* Naringenin
* Navacaprant
* Norbinaltorphimine
* Noribogaine
* Pawhuskin A
* PF-4455242
* RB-64
* Quadazocine
* Taxifolin
* UPHIT
* Zyklophin

Nociceptin
(NOP)|

| Agonists|

* (Arg14,Lys15)Nociceptin
* ((pF)Phe4)Nociceptin(1-13)NH2
* (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2
* Ac-RYYRWK-NH2
* Ac-RYYRIK-NH2
* BU08070
* Buprenorphine
* Cebranopadol
* Dihydroetorphine
* Etorphine
* JNJ-19385899
* Levomethorphan
* Levorphanol
* Lexanopadol
* MCOPPB
* MT-7716
* NNC 63-0532
* Nociceptin (orphanin FQ)
* Nociceptin (1-11)
* Nociceptin (1-13)NH2
* Norbuprenorphine
* Racemethorphan
* Racemorphan
* Ro64-6198
* Ro65-6570
* SCH-221510
* SCH-486757
* SR-8993
* SR-16435
* Sunobinop (S-117957)
* TH-030418

|

Antagonists|

* (Nphe1)Nociceptin(1-13)NH2
* AT-076
* BAN-ORL-24
* BTRX-246040 (LY-2940094)
* J-113397
* JTC-801
* NalBzOH
* Nociceptin (1-7)
* Nocistatin
* SB-612111
* SR-16430
* Thienorphine
* Trap-101
* UFP-101

Others|

* Enkephalinase inhibitors: Amastatin
* BL-2401
* Candoxatril
* D-Phenylalanine
* Dexecadotril (retorphan)
* Ecadotril (sinorphan)
* Kelatorphan
* Racecadotril (acetorphan)
* RB-101
* RB-120
* RB-3007
* Opiorphan
* Selank
* Semax
* Spinorphin
* Thiorphan
* Tynorphin
* Ubenimex (bestatin)

* Propeptides: β-Lipotropin (proendorphin)
* Prodynorphin
* Proenkephalin
* Pronociceptin
* Proopiomelanocortin (POMC)

* Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[5-HT1AR]: 5-HT1A receptor
*[GABAAR]: GABAA receptor
*[PAMs]: positive allosteric modulators
*[α2δ]: alpha2delta subunit
*[VDCC]: voltage-dependent calcium channel
*[SSRIs]: Selective serotonin reuptake inhibitors
*[SNRIs]: Serotonin-norepinephrine reuptake inhibitors
*[SARIs]: Serotonin antagonist and reuptake inhibitors
*[TCAs]: Tricyclic antidepressants
*[TeCAs]: Tetracyclic antidepressants
*[MAOIs]: Monoamine oxidase inhibitors